This project proposes a stereoselective total synthesis of chartelline A, a marine natural product with a unique pentahalogenated hairpin-like structure consisting of a ten-membered macrocycle with fused indole, imidazole, and beta-lactam heterocycles. This structure has never been synthesized previously. The proposed synthetic route features a novel amidyl radical macrocyclization, followed by the stereoselective introduction of the beta-lactam by an interesting tandem reaction driven by the double elimination of a cyclic phosphate. Thus, the synthesis of chartelline A will enable the investigation of novel reaction methodology and synthetic strategies. Additionally, the synthesis of chartelline A will allow the study of the biologic activity of this type of structure. The biologic function of chartelline A is unknown; however, the structure suggests that chartelline A may be a reactive natural product that covalently links with a biologic target. The synthesis of chartelline A will prepare material for further biologic testing including proteomics screening to identify human proteins that may react with this structure.